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20-September-2008 09:55:46 - Amphotericin B Amphotericin B Systematic IUPAC name 1R-1R,3S,5R,6R,9R,11R,15S,16R,17R, 18S,19E,21E,23E,25E,27E,29E,31E,33R, 35S,36R,37S-33-3-Amino-3,6-dideoxy-beta- D-mannopyranosyloxy- 1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl -13-oxo-14,39-dioxabicyclo33.3.1nonatriaconta- 19,21,23,25,27,29,31-heptaene-36- carboxylic acid Identifiers CAS number 1397-89-3 ATC code A01AB04 A07AA07, G01AA03, J02AA01 PubChem 14956 DrugBank APRD00797 Chemical data Formula C47H73NO17 Mol. mass 924.084 Pharmacokinetic data Bioavailability 100% IV Metabolism renal Half life initial phase : 24 hours, second phase : approx. 15 days Excretion 40% found in urine after single cumulated over several days biliar excretion also important Therapeutic considerations Pregnancy cat. BUS Legal status Rx-only, hospitalization recommended. Routes slow i.v.-infusion only Amphotericin B Fungilin, Fungizone, Abelcet, AmBisome, Fungisome, Amphocil, Amphotec is a polyene antifungal drug, often used intravenously for systemic fungal infections. It was originally extracted from Streptomyces nodosus, a filamentous bacterium, in 1955 at the Squibb Institute for Medical Research from cultures of an undescribed streptomycete isolated from the soil collected in the Orinoco River region of Venezuela. Its name originates from the chemical's amphoteric properties. Two amphotericins, Amphotericin A and Amphotericin B are known, but only B is used clinically because it is significantly more active in vivo. Currently the drug is available as plain Amphotericin B, as cholesteryl sulfate complex, as lipid complex, and as liposomal formulation. The latter formulations have been developed to improve tolerability for the patient but may show considerably different pharmacokinetic characteristics compared to plain Amphotericin B. Contents 1 Uses 2 Mechanism of action 3 Side effects 4 Interactions 5 Liposomal and lipid complex preparations 6 External links Uses Oral preparations of Amphotericin B are used to treat thrush; these are virtually nontoxic, in contrast to typical I.V doses. The main I.V use is in treating various systemic fungal infections e.g. in critically ill, comorbidly infected or immunocompromised patients, and as a drug of last resort in otherwise untreatable parasitic protozoan infections such as visceral leishmaniasis and primary amoebic meningoencephalitis. It is also used empirically as a heroic measure in febrile immunocompromised patients who do not respond to broad-spectrum antibiotics. Mechanism of action As with other polyene antifungals, amphotericin B associates with ergosterol, a membrane chemical of fungi, forming a pore that leads to K+ leakage and fungal cell death. Recently, however, researchers found evidence that pore formation is not necessarily linked to cell death i.e. Angewandte Chemie Int. Ed. Engl. 2004. The actual mechanism of action may be more complex and multi-faceted. Amphotericin B is believed to interact with membrane sterols ergosterol to produce an aggregate that forms a transmembrane channel. Intermolecular hydrogen bonding interactions among hydroxyl, carboxyl and amino groups stabilize the channel in its open form, destroying activity and allowing the cytoplasmic contents to leak out. Side effects Amphotericin B is well-known for its severe and potentially lethal side effects. Very often a serious acute reaction after the infusion 1 to 3 hours later is noted consisting of high fever, shaking chills, hypotension, anorexia, nausea, vomiting, headache, dyspnea, and tachypnea. This reaction sometimes subsides with later applications of the drug and may in part be due to histamine liberation. An increase in prostaglandin-synthesis may also play a role. This nearly universal febrile response necessitates a critical and diagnostically difficult professional determination as to whether the onset of high fever is a novel symptom of a fast-progressing disease, or merely the induced effect of the drug. In order to decrease the likelihood and severity of the symptoms, initial doses should be low and increased slowly. Acetaminophen, pethidine, diphenhydramine and/or hydrocortisone have all been used to treat or prevent the syndrome, but the prophylactic use of these drugs is often limited by the patient's condition. Intravenously administered Amphotericin B has also been associated with multiple organ damage in therapeutic doses. Nephrotoxicity kidney damage is a frequently reported side-effect, and can be severe and/or irreversible. It is much milder when delivered via liposomes AmBisome if possible. Electrolyte imbalances e.g. hypokalemia and hypocalcemia may also result. In the liver, increased liver enzymes and hepatotoxicity up to and including fulminant liver failure are common. In the circulatory system, several forms of anemia and other blood dyscrasias leukopenia, thrombopenia, serious cardiac arrhythmias including ventricular fibrillation, and even frank cardiac failure have been reported. Skin reactions, including serious forms, are also possible. Interactions Flucytosine : Toxicity of Flucytosine increased and vice versa Diuretics or Cisplatin : Increased renal toxicity and incrised risk of hypokalemia Corticosteroids : Increased risk of hypokalemia Cytostatic drugs : Increased risk of kidney damage, hypotension and bronchospasms. Other nephrotoxic drugs : Increased risk of serious renal damage. Monitor patients closely. Foscarnet, Ganciclovir, Tenofovir, Adefovir : Risk of hematological and renal side-effects of Amphotericin B increased. Transfusion of Leukocytes : Risk of pulmonal lung damage. Space intervals between the application of Amphotericin B and the transfusion and monitor pulmonary function. Liposomal and lipid complex preparations From studies it appears that liposomal amphotericin B preparations exhibit fewer side-effects while having similar efficacy. Various preparations have recently been introduced. All of these are more expensive than plain Amphotericin B. AmBisome is a liposomal formulation of amphotericin B for injection, developed by NeXstar Pharmaceuticals acquired by Gilead Sciences in 1999. It is marketed by Gilead in Europe and licensed to Astellas Pharma formerly Fujisawa Pharmaceuticals for marketing in the USA, and Sumitomo Pharmaceuticals in Japan. Fungisome is a liposomal complex of Amphotericin B and being the latest and cheapest addition to the lipid formulations of Amphotericin B has many advantages. It is marketed by Lifecare Innovations of India. Other formulations include Amphotec Intermune and Abelcet Enzon Pharmaceuticals. Abelcet is not a liposomal preparation but rather a lipid complex preparation. External links Fungisome web site run by Lifecare Innovations AmBisome web site run by Astella Pharma Special issue 2005. Journal of Postgraduate Medicine 51 Suppl. v d e Stomatological preparations A01 Caries prophylactic agents Sodium fluoride - Sodium monofluorophosphate - Olaflur - Stannous fluoride Anti-infectives and antiseptics Hydrogen peroxide - Chlorhexidine - Amphotericin B - Polynoxylin - Domiphen - Oxyquinoline - Neomycin - Miconazole - Natamycin - Hexetidine - Tetracycline - Benzoxonium chloride - Tibezonium iodide - Mepartricin - Metronidazole - Clotrimazole - Sodium perborate - Chlortetracycline - Doxycycline - Minocycline - Eugenol Corticosteroids Glucocorticoids Triamcinolone - Dexamethasone - Hydrocortisone Other Epinephrine/Adrenalone - Benzydamine - Acetylsalicylic acid - Amlexanox v d e Antidiarrheals, intestinal anti-inflammatory/anti-infective agents A07 Intestinal anti-infectives Antibiotics Neomycin, Nystatin, Natamycin, Streptomycin, Polymyxin B, Paromomycin, Amphotericin B, Kanamycin, Vancomycin, Colistin, Rifaximin Sulfonamides Phthalylsulfathiazole, Sulfaguanidine, Succinylsulfathiazole other Miconazole, Broxyquinoline, Acetarsol, Nifuroxazide, Nifurzide Intestinal adsorbents Charcoal - Bismuth - Pectin - Kaolin - Crospovidone - Attapulgite - Diosmectite Antipropulsives opioids Diphenoxylate - Opium - Loperamide - Difenoxin - Paregoric - Laudanum - Codeine - Morphine Intestinal anti-inflammatory agents corticosteroids acting locally Prednisolone, Hydrocortisone, Prednisone, Betamethasone, Tixocortol, Budesonide, Beclometasone antiallergic agents, excluding corticosteroids Cromoglicic acid aminosalicylic acid and similar agents Sulfasalazine, Mesalazine, Olsalazine, Balsalazide Antidiarrheal micro-organisms Saccharomyces boulardii Other antidiarrheals Albumin tannate - Ceratonia - Racecadotril v d e Antifungals D01 and J02 Ergosterol inhibitors Azoles CYP51A1 inhibitors topical: imidazoles Bifonazole, Clomidazole, Clotrimazole, Croconazole, Econazole, Fenticonazole, Ketoconazole, Isoconazole, Miconazole, Neticonazole, Oxiconazole, Sertaconazole, Sulconazole, Tioconazole triazoles Fluconazole, Fosfluconazole benzimidazole Thiabendazole systemic: triazoles Itraconazole, Posaconazole, Voriconazole Polyene antimycotics ergosterol binding topical: Natamycin, Nystatin systemic: Amphotericin B Allylamines squalene monooxygenase inhibitors topical: Amorolfine, Butenafine, Naftifine, Terbinafine systemic: Terbinafine 1,3-beta-glucan synthase inhibitors echinocandins Anidulafungin, Caspofungin, Micafungin Intracellular Pyrimidine analogues/ Thymidylate synthase inhibitors Flucytosine Mitotic inhibitors Griseofulvin Others Ciclopirox Ethylparaben Salicylic acid Selenium sulfide Tolnaftate Undecylenic acid Tea tree oil citronella oil lemon grass orange oil patchouli lemon myrtle Whitfield's ointment v d e Gynecological anti-infectives and antiseptics G01 Antibiotics polyene antimycotic Nystatin, Natamycin, Amphotericin B - Candicidin - Chloramphenicol - Hachimycin - Oxytetracycline - Carfecillin - Mepartricin - Clindamycin - Pentamycin Arsenic compounds Acetarsol Quinoline derivatives Diiodohydroxyquinoline - Clioquinol - Chlorquinaldol - Dequalinium - Broxyquinoline - Oxyquinoline Organic acids Lactic acid - Acetic acid - Ascorbic acid Sulfonamides Sulfatolamide Imidazole derivatives Metronidazole - Clotrimazole - Miconazole - Econazole - Ornidazole - Isoconazole - Tioconazole - Ketoconazole - Fenticonazole - Azanidazole - Propenidazole - Butoconazole - Omoconazole - Oxiconazole - Flutrimazole Triazole derivatives Terconazole Other Clodantoin - Inosine - Policresulen - Nifuratel - Furazolidone - Methylrosaniline - Povidone-iodine - Ciclopirox - Protiofate - Lactobacillus fermentum - Copper usnate Retrieved from http://en..org/wiki/Amphotericin_B Categories: Gilead Sciences | Antifungals | Polyketide antibiotics Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Français Italiano Magyar 日本語 Polski Português 中文 This page was last modified on 17 August 2008, at 08:09
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